How to Sell by Tyler Bosmeny
Summary
TLDRTyler Bosmeny, CEO of Clever, shares his experiences and insights on sales and the sales process for early-stage startups. He discusses key aspects like prospecting for potential customers, having meaningful conversations to understand their needs, persistence in following up, avoiding common closing traps, and tailoring your sales approach based on your business model. Throughout, he emphasizes the importance of listening, building relationships, and providing genuine value to customers. While sales has mystique, Bosmeny argues founders themselves can excel at it early on through passion, expertise, hustle and learning from experience.
Takeaways
- 😊 Sales is a core responsibility for founders, not just for salespeople
- 👂 Sales is about listening and understanding the customer's needs
- 🚪 Use your network, conferences, and cold emails to find prospects
- 📞 Have quality conversations focused on the customer, not just pitching
- ⏳ Sales requires persistence and systematic follow-up
- 💰 Avoid common closing traps like over-negotiating contracts
- 🎯 Align your sales model to your target customer and pricing
- 😀 Leverage your passion and expertise as advantages in sales
- 🤝 Build genuine relationships and provide value to customers
- 👥 Ultimately you need enough happy customers to sustain business
Q & A
What are some key advantages founders have when it comes to sales?
-Founders have two key advantages - passion and industry expertise. Their passion for their product is unmatched, and they understand the problem it solves better than anyone.
What percentage of companies fall into the 'innovator' category according to the technology adoption lifecycle?
-Only 2.5% of companies are considered innovators - those willing to take a chance on an unproven startup. This means you need to cast a wide net and reach out to many companies to find potential early adopters.
What makes conferences a powerful way to meet potential users?
-At conferences, users are gathered with their peers and focused on learning. Having the attendee list in advance allows you to set up meetings and introduce your product more effectively than cold outreach.
What is the most important skill for sales according to the speaker?
-Listening. The best salespeople spend more time listening and asking questions rather than talking about their product. Understanding user needs is crucial.
How can founders avoid getting bogged down during contract negotiations with early customers?
-Don't quibble over small details, especially with your first few customers. Getting those initial customer commitments and revenue is vital, so focus on closing quickly.
What are some common closing traps to avoid with potential customers?
-Avoid building custom features for a single customer, providing free trials instead of paid commitments, and letting the sales cycle drag on for too long.
How many touchpoints did it take to close one of the speaker's early deals?
-The example showed over 15 touchpoints ranging from emails to calls and demos. Persistence and systematic follow-up is key.
How should founders determine the right sales model for their business?
-Consider whether you need to land a few large customers vs. many small ones. Then build a sales process sustainable for that number and price level.
When is the right time for a startup to hire sales reps?
-Not until the founders have done substantial sales themselves first. Otherwise you won't know what to look for in candidates.
What traits should startups seek out in early sales hires?
-Energy, passion, and 'Renaissance' skills - ability to figure things out without much structure or collateral.
Outlines
🎤 Introduction & context for the startup school talks this week
Adora says they're halfway through startup school. Tyler from Clever will talk about how to sell products. Harsh and Amin from Triplebyte will discuss building engineering organizations. Adora asks everyone to fill out the midpoint feedback form to help improve startup school. She advises carefully choosing metrics that truly measure progress towards success.
🗣 Tyler introduces himself and the value of mastering sales
Tyler from Clever introduces himself. He explains sales is fundamental but often misunderstood with a mystique around it. He details his accidental path into sales via running ads for his college newspaper. He now recognizes sales as an important craft. He advises founders not to wait to hire salespeople because selling is their responsibility.
📈 Tyler outlines the sales funnel from leads to revenue
Tyler diagrams the sales funnel: prospecting leads, having conversations to gauge fit, closing deals, and hopefully gaining revenue. He says founders should have a team member fully focused on sales. For prospecting, he recommends leveraging networks, conferences, and thoughtful cold emails to efficiently find the few potential customers.
🎟 Conferences are an underrated place to meet engaged users
Tyler advocates conferences as the most underrated but amazing places to meet highly engaged potential users. He details how to identify the right conferences, get attendee lists, and efficiently book meetings at them. He calls conferences the most productive days for understanding customers and demand.
👂 Sales is mostly about listening, not charming persuasive pitches
Tyler stresses the most important sales skill is listening deeply to understand user problems and needs. He observes most founders pitch eagerly without enough listening. The best salespeople listen 70% of the time. This builds relationships and trust to uncover how your solution can uniquely help.
❌ Sales has many steps and requires tireless follow-up persistence
Tyler shows an example sales process taking months across many communications. Sales requires relentless follow-up persistence, not just a single call. Be embarrassingly persistent to keep doors open, while still carefully listening.
🤝 Move quickly when negotiating early customer agreements
Tyler advises finalizing agreements with early potential customers as quickly as possible. Their validation is invaluable so don't quibble over minor details, but get the first sales closed expeditiously.
💡 Tailor your sales approach to target customer lifetime value
Tyler explains sales strategy must fit the number of customers needed and revenue per customer. High-touch sales fits high-value customers but low-value customers need scalable self-service. Align sales approach to target customer lifetime value.
😊 Concluding thoughts and offer for questions
Tyler wraps up with key lessons learned. He encourages trying sales yourself as the best way to learn. He offers to answer any questions from the audience.
🤔 Answering audience questions about sales
Tyler fields audience questions on appropriate sales follow-up timing, signs of product/market fit, balancing large & small customer references, determining pricing, low-touch sales for low-value products, and when and how to hire salespeople.
Mindmap
Keywords
💡sales
💡prospecting
💡conferences
💡listening
💡follow-up
💡closing
💡first customers
💡sales model
💡pricing
Highlights
Sales has a lot of mystique and lore around it, but in reality it's about listening, building relationships and understanding people's problems.
As founders, you have advantages in sales - your passion and expertise. So don't think you can't do sales even if you've never done it before.
Conferences are hugely underrated for sales. Go where your users are - find the big conferences in your industry and use them to set up meetings.
When you finally get a prospect on the phone, remember to shut up and listen. Listening is the number one sales skill.
Sales is a relationship-driven process with lots of steps. Be prepared to follow up relentlessly - it's normal for even interested prospects to fall through the cracks.
Avoid common closing traps like building one-off features, offering free trials instead of paid pilots, or letting legal kill deals over minor issues.
Match your sales model to your business model based on average deal size. Going from 0 to $1M requires a very hands-on approach.
Use your network to find early prospects. Ask friends and friends of friends if they know of good targets.
Cold emails should be short, personalized and actionable - just trying to start a conversation.
Don't spend time building one-off features for individual prospects - make clear it has to be something you were going to build anyway.
First sales hires should be "Renaissance reps" - scrappy generalists who can figure it out, not specialists who need extensive support.
Don't hire any salespeople until you've done significant sales yourself - otherwise you won't know what to look for.
Use data from your calls to improve - if you dominated the conversation, that's bad. Good sales calls have a 70/30 listen/talk ratio.
Treat early customers like gold - make concessions and close deals quickly rather than losing them by being inflexible.
Pricing is a guessing game - throw out a number, see if you can close it, then double it until you find resistance. Don't be afraid to charge more.
Transcripts
all right good morning everyone we are
halfway through startup school can you
believe it already Wow yeah or more
correctly we will be after this week and
this is going to be a great week of
talks lectures conversations today we
have Tyler from clever who's going to
give a talk on how to sell to begin with
and after words harsh and Amin from
triple bite are going to talk about how
to build an engineering organization to
pretty important things if you want to
build a successful company I will start
off quickly with my usual administrivia
we will shortly be sending out a mid
point feedback form for you guys to fill
out we really will appreciate getting as
many responses as possible this is our
form of talking to our customers you all
and getting feedback we're always trying
to improve startup school we hope to do
it every year and make it better every
year
so please tell us what you think and
what you think we should change adora
and i we're talking a little bit about
updates and I've talked to a bunch of
people alive and some on the forum about
about updates and and what makes sense
for updates and just to put it bluntly
think hard about your metrics the ones
you're using do not use metrics
what is a metric it's a metric
that doesn't really measure the road to
success for you it's something you're
making up any startup that you're
building is an enormous complicated
difficult crazy task and no matter what
you're doing if there is no mile stone
on the way to that to achieving that
enormous task then you're kidding
yourself and you're not really a step on
the way to success those milestones are
more than anything for you for you to
measure that you're making progress
towards your goal so don't make stuff up
because you think that's what we want to
hear or just because you're bored
it won't help you okay
as always problems etc email to start-up
school at Y Combinator calm and with
that I think Tyler we are ready to go so
my good friend Tyler basmati from clever
hey everyone it's an honor to be here I
was speaking with you today thanks for
having me
my name is Tyler basmati I'm the CEO of
a company called clever and I wanted to
talk to you about something that I think
is one of the most fundamental and
important things any founder needs to
master which is sales and before I get
started and share some of the things
I've learned and picked up over the way
I thought it might be helpful to share
my own personal journey to sales as
something that I've come to learn and
just you know really appreciate and
respect as a craft when I was in school
when I was in college I was a math major
my you know my graduate degree was in
statistics I was the last person I ever
thought would ever do sales and so my
own journey to getting here was I was
working on the college newspaper I
joined the college newspaper it seemed
like a fun thing to do had some friends
who are on it and one of the roles they
had open was they needed somebody to run
the advertising for the newspaper and so
I was spending in college hours a day
you know figuring out how to sell ads to
local businesses so we'd have enough
money to print and put out the paper
every day and over the doing this for
several years if you know anything about
college newspapers you know one of the
things the biggest determinant of how
much money they make every year is how
well the economy is doing it's a lot of
the ads are for recruiters but B I just
happened to be there during some very
good years and when I was leaving the
advertising sales team we had we set
records for the Crimson and so we just
you know we sold a lot of ads and so I
thought okay this is interesting you
know it's
it's an interesting craft and then as I
was getting ready to graduate school you
know getting ready to graduate go off to
college or excuse me golf to work you
know I'm doing math I'm thinking to go
off to finance do a hedge fund something
like that a buddy's starting a company
and he says to me Tyler I need you to
come join because you're the only person
I know who knows how to do sales and let
me tell you I was offended like this was
not how I saw myself this was not you
know what I imagine doing after school
but I was also really intrigued and I
was really good friends with this guy
and I said oh you know why the heck not
so ended up on going on a very different
path and joining his startup building a
sales team you know we were selling to
newspapers across the country and if
you've ever worked with or or thought
about newspapers before you can imagine
they are very hard customers to sell to
and so I really cut my teeth and have a
lot of fun frankly over many years
figuring out how to sell into this
market and we sold to a lot of
newspapers then fast-forward a little
bit and I come on to start clever and
one of the co-founders started through Y
Combinator about six years ago
and if you don't know anything about
clever you know we're a single sign-on
platform used in schools and today over
half the schools in America use clever
and so we've really done a lot of
selling and really had to figure this
out once again in a different context
and so I was thinking about you know
what would be most helpful to talk about
what I'd most want to hear in your shoes
or what I most would have appreciated
knowing when I was first starting to cut
my teeth on sales and so that's what I
want to share with you today it's just
things I've picked up along the way
some observations I've had and hopefully
some practical tips that you can take
home and implement you know as you get
your startups off the ground running
sales sales has a lot of mystique and a
lot of lore around it or at least it did
to me when I was thinking about sales
early in my career you know when we
think about sales and we think about
people you know a lot of us picture Don
Draper we picture these people who are
so charming so impossibly funny who they
always have the right line at the right
moment you know to win the deal this you
know they're of course incredible
golfers this is how sales is portrayed
in every movie in every TV show and so a
lot of people go through life thinking
that this is what sales is about and
because we have we build up this
mystique of what sales is and the types
of people who can do sales
I hear founders say very often things
like well right now we're just building
the product and once it's finished you
know then we'll go and hire the
salespeople well guess what hire the
salespeople that's you
and it's that looks nothing like the
mystique and it looks nothing like the
lore in my experience you know this is
my co-founder Dan in the early days of
clever and we were doing sales you know
here he is on a broken chair in a three
by three call room I think he's eating a
bagel because he probably didn't have
time for breakfast that's what sales
looks like you know could not be further
from the Don Draper imagery that a lot
of people think of so sales is you and
you know Y Combinator
Paul Graham I remember when we were
going through the program Paul Graham
got up on this stage and he said you
should be spending every moment of every
day doing one of two things building
your product are talking to users and
talking to users a big part of that can
be selling so this is a core
responsibility of every startup founder
is not just building the product but
also talking to your users understanding
their needs and as you'll learn that is
really a big part of what selling is so
this is a core responsibility for
founders you know a lot of founders
think well I haven't done sales before
and that's true and they say well I'm
not good at sales yet and that could be
true too but one thing I've learned is
that as founders you also have some very
unique advantages that will that can
make you actually
the powerful at sales and very potent
and the two advantages that I've noticed
one is just your passion you are more
passionate about the product that you're
building and selling than anyone in the
world because otherwise you probably
wouldn't have irrationally quit your
jobs and moved in with your parents or
whatever you've done to start this
company so one is your passion that is
so powerful in sales and the second
thing you have is industry expertise you
know this problem better than anyone you
know why it needs to exist you
understand this problem more deeply
hopefully than anyone and so these two
things even if you've never done sales
before I mean you can be incredibly
effective and so don't think otherwise
early on with clever one of the things
we did that really worked for us was I
had two co-founders so there were three
of us and we just decided that one of us
had to own sales it was so important
that we needed one person to be thinking
about this every day and so that ended
up becoming me my other two co-founders
were focused on building the product and
implementing the product and I folk I we
decided this was important enough that I
decided I was gonna peel off and spend
almost a hundred percent of my time
selling this product starting from
before it was even built so from that
point you know from early enough on
think about who and your company is
really owning this and it should
probably be a founder and it should
probably be as much of a full-time job
as you can spare so now I want to talk
about how sales actually works and if
you know anything about sales you know
sales 101 as a lot of people talk about
it like a funnel and there's different
variations of this funnel I have a
really simple one that I put up here
step one of the funnel is finding
prospects prospecting these are leads
who might even be interested in buying
your product who might even be
interested in taking a call from there
you have conversations okay so you
figured out they're interested but you
got to have a lot of conversations to
figure out is this the right product for
them
or not third is closing okay you
actually they actually want to buy the
product how
do not snatch defeat from the jaws of
victory and lose the deal oh yes to go
through a closing process and if you
complete all of those things then
hopefully you are in the promised land
and you have revenue when you have your
first sales and so this is how I think
about the funnel and what I'm gonna do
now is just walk you through each of
these stages and share how I've
approached these in my career and some
tips that have worked for me along the
way so your mission in the first stage
of prospecting it's to figure out who
will even take your call and one of the
things that for me was really helpful to
understand is well you're gonna hear
know a lot you're talking you you start
talking about a new product people and
you're just gonna hear a lot of nose but
one of the things that was really
helpful for me to understand is you have
this technology adoption curve this was
put out by a guy Everett Rogers in the
60s and it starts on the left you have
your innovators then you have your early
adopters of new technology or early
majority your late majority your
laggards these are terms that people in
Silicon Valley throw around that I'd
been hearing for years but what I didn't
know was that the inventor of this
framework this technology adoption
lifecycle Everett Rogers he describes it
as a bell curve and he actually went
through the effort of quantifying the
area under the curve in each of these
different segments and one of the things
and so one of the things you notice is
looking at this the innovators segment
is just 2.5 percent of the population
that means 2.5 percent of companies will
will even consider buying a product from
a startup that is unproven with no
revenue and when you realize that - some
founders that's kind of depressing like
wow that's a very small percent of the
market but when I found this out I
actually found it massively motivating
and massively invigorating because all
of a sudden it makes what you have to do
really clear you have to talk to you a
lot of people because you have to find
that 22.5% it's a numbers game means
you're gonna have to reach out to
Atlee
200 companies to find just two and a
half on average who are even in you know
potential buyers for your product you're
basically playing like a version of
Where's Waldo you know where you're
looking for the you know the very few
companies who might be in this innovator
segment and so expect early on sales is
not reaching out to a you know two four
ten companies reaching out to sale
reaching out and doing sales is a lot of
grinding and it's a lot of effort in
order to get the result you want when it
comes to actually starting these
conversations I found there's three
things that work for me so in terms of
finding those innovators the first thing
that work has worked well for me is
using my network the second which is a
little surprising to people is
conferences and I'm going to talk about
that and the third is cold emails these
are the three ways in which I find
prospects I'm not going to talk about my
networks I think most people understand
that but I can tell you many of the
earliest deals I've done it every
company I've been at have been through
people I've known friends of friends so
do not underestimate your network
especially if you know the industry you
might think it's not very big but you
probably know a few people and those
people might know a few people and so
spend some time thinking about your
network because you might find some
really great sales opportunities that
come through there and those are the
best you don't need a hundred people in
your network to get to sales you can
usually do it with much fewer but let's
talk about conferences because I think
conferences are the most underrated
aspect of sales and them and one of the
least understood aspects of sales
when I say conferences a lot of people
think I'm talking about this like CES or
e3 and going you know it's at some place
where there's 80,000 people and it's
basically more like a rock concert than
you know then it's than anything else
and when I say conferences I'm talking
about something very different
usually they look like this usually it's
a bunch of you know executives or
people in a hotel room cooped up for a
couple days you know oftentimes you know
in places like Milwaukee or Kansas and
let me tell you this is such a powerful
way these conferences are such a
powerful way to meet your users you have
to go where your users are and many
times if you're selling to a business or
to a corporate buyer this is where users
are they go to conferences they're there
with their peers they're learning and
that's where you should be - now let me
say a few words about how I've
approached conferences in the past
because this this really is where so
many of clevers initial partnerships and
customers came from one figure out what
are the big industry conferences for
your product in your startup usually
there's not just one usually there's
like 10 and you have to work to figure
out what they are ask people in the
industry where do you what conferences
do you go to which ones do you you know
are on your radar but there's usually
quote there's usually quite a few in
definitely more than one - pick a few
that you're going to attend buy a ticket
sometimes they're expensive you know
thousands of dollars sometimes you don't
even need a ticket you know depends on
the event but figure out the conference
and decide you're gonna go hopefully
weeks or months in advance three get the
conch get the list this is such an
important part of making conferences
like this worthwhile find a way to know
who's gonna be there write to the
organizers write to sponsors you know
maybe it's on the website but figure out
who's gonna be there in advance don't
just show up at a conference and think
you're gonna like network your way and
meet everybody although if you can pull
that off by all means do it it's just
not something that that everyone can do
but when you have the list of who's
gonna be there then you can email people
in advance and say hey you know I'm
gonna be at this event I noticed you
were - I'm working on this thing I'd
love to show it to you can we find some
time to chat and don't just do it with a
few people do it with his men
potential buyers or prospects as you can
my goal when I go to a conference or
when anyone from clever goes to a
conference is that we have our entire
days booked up in 30-minute increments
because we've done so much effort in
advance of the conference's trying to
line everything up getting these
meetings and they end up becoming the
most productive day of the year when we
actually go and we actually get to have
all of these conversations and have all
of these buyers and I get to the end of
a night even the first night at a
conference when yeah just been doing one
day and let me tell you every time I am
exhausted and I am also so energized
because there's nothing that's more fun
than meeting with customers and meeting
with potential buyers and hearing their
reactions to what you're building so I
cannot emphasize enough how important
conferences have been in every aspect of
in every company I've worked in sales at
and I highly recommend you explore this
so that's conferences the other and
frankly the you know more probably more
common approach is called emails people
don't really cold call too much anymore
maybe you could make it work but cold
emails I mean I still do that today and
and a lot of people are don't know how
to write cold emails they don't know how
to you know reach out to someone in a
productive way I know this because I'm
on the receiving end of so many bad cold
emails we probably all are they're
really long they're not personalized or
not actionable they're boring they're
irrelevant so don't do that but if you
don't do that like well then what do you
do how do you have a cold email you know
strategy that's effective in the early
days of clever in the early days of
other startups we would sit and sit down
and we'd send you know 10 30 50 emails
to cold prospects and it would look
something like this and I've actually
found an old email and I put it up here
so you guys can see it you feel free to
copy it but it is the simplest thing in
the world
you'll notice it's short it's to the
point it's personalized it's actionable
hey my name is Tyler and I'm the CEO of
clever this is you know what we do I
thought this might be rel
for you because of XYZ reason that's you
know personal to you
even if you're not in the market I'd
love to chat with you about this which
is true do you have some time this week
later this week I'm free I'm free now or
you know I'm free at this time super
simple super you know this will probably
get read as opposed to some of the
paragraph long you know diatribes about
why my product is the best and why
you're crazy for not using it and before
we've even met
all you're trying to do is get a call
with somebody and actually meet them and
so we'll send out cold emails it's it's
very effective but you know make sure
you do it right make sure you're writing
emails that are interesting to people
that aren't too salesy that are
personalized and that are genuine and
remember all you're trying to do is get
a conversation get it out of that
prospecting phase and into stage two
which is conversations so let's talk
about stage two stage two okay if you've
gone to conferences you've done cold
emails you've worked your network and
now you're talking to prospects this is
exciting people want to talk to you they
might want to buy your product this is
what you've been waiting for when this
happens and you get them on the phone
remember to shut up and listen and when
people ask me you know what's your
number one sales tip what's the number
one when new sales people say what's the
number one thing I should practice or
work on if you take nothing else from
this presentation take this sales is
about listening I've had the opportunity
in my life to shadow some of what I who
I think are some of the best salespeople
in the world
incredibly successful salespeople and
they look nothing like the picture I
showed you on the first slide you know
they were soft-spoken they and what I
remembered specifically was that they
were world-class listeners and the
reason that's so important is because
that's what sales is at its core people
think sales is about just you know you
know like a being a battering ram and
just hitting you're getting your points
across and repeating them over and over
until somebody finally you know breaks
down
by your product and let me tell you that
doesn't work and what does work is is
building relationships with people
understanding their problems
understanding what their needs are and
then seeing if you can help them with
your solution and in order to make that
happen
you have to listen so most founders when
I I've shadowed a lot of sales calls and
I one thing I see very frequently is a
founder they're so excited they finally
got someone on the phone they're hooked
they're definitely gonna be the first
customer and they get them on the phone
and they just talk and it's
understandable right you're excited
you're excited that you know about your
product you're passionate about it you
can't wait to show off every bell and
whistle but you've spent months
thoughtfully building but it will
totally kill your sales your sales deal
what you'll naturally do is talk for
seventy percent of the time on the first
call and you know maybe leave 30 percent
of space for the other person the best
sales people in the world when I've seen
them in action it's the opposite they're
listening 70 percent of the time and
they're asking questions like hey tell
me about the problem you're having how
do you solve it today why did you even
agree to take my call what would your
ideal solution look like if you could
have anything they're asking questions
because they care and they want to
understand and they want to figure out
how to help this person solve their
problem and yes their product might be
part of that solution but it involves
deep listening you know we have one one
trick I can share on this is we at
clever we use a tool called uber
conference and every conference is great
but one of the things I love about it is
at the end of each call it sends you an
email and it tells you how much time you
spent talking versus how much time the
other person spent talking and it's
funny because I can look at these and
it's a running joke I'll look at these
in you know sometimes you'll talk to
someone and say I just got off a call it
was great I nailed it you know where
they're gonna definitely buy and then
I'll look at the Eber conference you
know call email
at the end then if it looks like that
I'll say I don't think that call went as
well as you think I don't know if we're
really you know ready to make that sale
quite yet and so the number one thing
that I hope to impress on you today is
sales is about listening and it's not
just about you know a hacker you know
asking the right questions it's about
genuinely listening and if you can do
that the rest is easy it really is so
you've got them on the you've you've
spent all this time prospecting you've
now even had your phone calls you've
done a good job listening and then one
thing another thing to know about sales
is there's a lot of steps to the process
you know up here I have a lot of
different steps that you might go
through in a sales process calls emails
pricing calls you know sending
references talking with different
executives there are a lot of steps to
sales and up here these aren't these
aren't just steps hypothetical steps
what I've put up here are actually all
of the steps from one of my very first
deals at clever this is one deal and
frankly some of the stuff is kind of
embarrassing right like met the person
they were interested I emailed no
response I emailed him again no response
I emailed him again they responded I
scheduled a call email no response I
mean this is straight-up embarrassing
and this is from someone who wanted to
buy our product isn't that crazy
so one of the things I hope to impress
on you is it is a lot of work to do
sales well and it takes a lot of
follow-up and you kind of have to have
this inhumane like willingness to just
keep going and push through this this
whole lifecycle probably took about two
months it ended up we ended up closing a
hundred thousand dollar-a-year customer
but this is what it took and I I talked
to a lot of founders who maybe they have
a good meeting they do a follow-up email
and
they don't get a response and they're
like oh well maybe they weren't
interested after all maybe it's not a
good fit and they disqualify themselves
well just remember this is what a
success case looks like at least if
you're doing enterprise sales and you
know it's not over till it's over and
it's not over till they say no but
sometimes you do have to kind of remind
them you know hey I'm still here hey are
you still interested because probably
your buyers have a lot on their mind
that's not you or your startup and
probably they have a lot of other things
going on in their life and so being
persistent isn't rude being persistent
can be helpful if you do it in the right
way and you're respectful now I will say
one thing here follow-up is really good
and really important but what's also
really good sometimes you get to know
and getting those noes can also be
really good and really helpful because
when you're a small startup with this
you know founder small founding team
you've got to figure out where to spend
your time and energy and you can't have
a pipeline of hundreds and hundreds of
deals going at one time you just can't
you you won't be able to do it and so
there's actually a lot of value my
friend Steve Garrity taught me this
there's a lot of value to driving
conversations to a yes or no quickly
because knows you can move on and get
and start filling the pipeline with
other people that could become yeses so
I would encourage you to have relentless
follow-up you know be determined go you
know don't let don't let things drop but
at the same time if you get a know you
know see it as a as a as a blessing in
disguise because you can move on to the
next deal that could be a yes okay so
you've prospected you've had these great
conversations with customers you've you
know made it through the rigmarole
you've gone through all these steps now
let's talk about closing this is an area
that it just it's weird it's foreign so
you have to figure out how to close a
contract with a customer who's told you
they want to buy it's harder than it
sounds a lot of deals get messed up in
here so let me just walk you through a
few things I've learned one assuming
you're doing a you know an enterprise
contract
you'll need an agreement and then you'll
send it over to the company and they'll
want to change the agreement though it's
a process called redlining and then
their lawyers will send it back to you
and you might look at it or your lawyers
might look at it you might have more
changes and you go back and forth in
this redlining process so the first step
is you need to have an agreement to
propose and by the way they're gonna
expect it from you they're gonna say
okay you know when they're interested
they're gonna say send me an agreement
and make sure that you have something or
you've been working on something so that
you know it's not like oh I'll get back
to you in a month if you don't have
something I've good news which is if
you're not aware YC has an open-source
sales template posted on their website
and I worked on this with James Reilly
it could when Proctor and some other
folks including the Y Combinator legal
team and wisely decided to open source
this so any of you can use it obviously
you'll probably need to customize it for
your needs and at some point you want to
get counseled but as this basic starting
point there's a free template that you
can use for sales and Y Combinator's
website and then once you have your
going into this back and forth I'll
never forget it I have seen some
founders let this process drag out for
months fighting over the dumbest things
when you are at an early stage startup
when you are trying to get your first
customers early customers are like manna
from heaven
they if you get and if you don't get
them you're not gonna go very far you're
done and yet I have seen startups in the
early phase because they think that what
they're supposed to do or someone gave
them bad advice quibble over the dumbest
things so my advice for you is when you
get to this step especially for your
first early customers they're gonna want
to put weird things in the contract with
indemnity clauses and warranty clauses
and don't say you know get it reviewed
by a lawyer don't sound anything dumb
but your goal is to finish and move on
and just keep that in mind and if you're
going through four or five six revision
processes you're doing something wrong
so figure out how to move this quickly
and don't quibble over small things
get get the first customers because
that's what you need to you know keep
going
okay another closing trap you got the
customer interested they want to buy
things look great and they come to you
and they say hey actually I want to buy
but only only if you had this one other
feature would I buy it sounds so
promising you're so close they just want
one more thing sure you can build that
thing it wouldn't be that hard
unfortunately once you start hearing
this in my experience unfortunately it
is more often a pass than anything else
and the thing to remember is
unfortunately building that one thing
when someone says oh I would buy it
except it's just missing that one thing
if you built it there might be there'd
probably be another thing after that and
another thing after that and you don't
want to be in a world where you're
building lots of one-off things for
customers now your first customer second
customer do what it takes folks but but
very quickly you get in a world where
you keep where you start hearing this
and you realize it's not a good thing
and so two ways I've seen of solving
this one is well if you really want the
sale and you really want to hold them to
their word and have that commitment say
okay well I'll build it if you if you
agree to you know figure aided by the
product which means I can't demo up for
you today I can't you know show you
reference customers on this thing you
want but I will build it for you if you
if you sign up and if you've spent the
time listening and building the
relationship and they trust you that can
work the other thing is you say look
we're gonna build what you know what
customers need and we're gonna wait till
we hear from four more customers and you
know oftentimes I find even in that case
if they still want the product they'll
buy it even without that one feature and
hopefully end up building what they need
anyways but but at least then you're not
building something for just one customer
third closing trap free trials you get
so close to someone they're so
interested there that your perfect first
customer and then they say yeah we just
like to try it for for 60 days folks
when you are starting your company and
when you are out there trying to
make your startup work you need things
like commitment you need validation you
need revenue and guess what a free trial
doesn't get you any of those things and
so I at every company I've been at I've
never worked at a company where they did
free trials we just said we can't do it
we're spending a lot of time out here
trying to find the right customers for
our product you're spending a lot of
time building the right product you know
we're not gonna we're not gonna give it
away for free on the hopes that maybe
you'll decide you want it but we flipped
it around and said but we want to be
reasonable and we know you're taking a
chance on us and you know there's risk
so we only do annual agreements here
that's our that's how we operate but if
for any reason you're not satisfied in
the first 30 days you can opt out of the
agreement and there won't be any penalty
and cancel and flip it and having it
that way where the default is they're a
customer but if something goes wrong
they're still protected actually meets
both part it's kind of both parties
meeting in the middle and it and it
solves for their concern that they're
taking a risk on someone new well not
while solving for your concern which is
that unique commitment and validation to
keep going and way better to be in a
case where the default is that they're a
customer then the default is well you
need to renegotiate something in 60 days
from now and you're right back where you
started so to the extent you can avoid
the free trial trap so that's closing so
now you know how I've approached
prospecting how I've approached the
conversations how I've approached
closing happy to answer questions on
these when we when we when we break but
just step end on some final parting
thoughts what I've described here is the
enterprise sales process I've used going
from 0 to 1 million first million in
revenue this is this is the exact
process we've used multiple times and
it's worked but not every company well
every company is different and one of
the things that I love to encourage
founders to think about early is what
kind of company and specifically what
kind of sales motion are you going to
have in the long term
Kristof chance who's a VC has this
really incredible blog post I just love
how memorable it is but he says there's
five ways to build a hundred million
dollar business from a sales perspective
if your average customer pays you a
hundred thousand dollars well then you
just need to find a thousand customers
and you're done or if your average
customer pays you ten thousand dollars
then you need to find ten thousand
customers and you're done or on the far
end so those are your elephants and your
deer on your far end he has these flies
and they only pay you ten dollars but
you need 10 million of them and so it
helps to think about as you're starting
to think about your sales motion well
how much are my customers paying and
therefore how many of them I gonna need
to have and what sort of sales motion is
going to be sustainable for my business
because if you're it's the way you're
selling your product today is you're
flying to people you're meeting them at
conferences you're doing everything I
touch you know I described this very
kind of high touch high energy sales
process but your customers are only
paying you $10 a year or $100 a year or
$1,000 a year and you're gonna have to
repeat that 10 million times it's
impossible it's it's impossible and it's
you know way too expensive
for you to build your business that way
on the other hand if you're successful
in building a low touch sales model
where you're able to do things you know
scalably maybe you're selling to small
businesses you know of which there's
millions maybe you have some way that
people doing self-service and sign up
well then you can be over on the right
side of this graph and you can have and
you can have a lower price product but
the price of your product and and your
sales motion are inextricably connected
and that's something that you know took
me a little while to understand but I
thought this graph really helped make
clear is depending on how much you're
able to charge for your product and
depending on how much people are willing
to pay for your product that'll change
how you approach sales as you're
building your company and building your
sales team so those are some lessons
I've learned along the way doing sales I
want it to end and just say good luck
out there
you know you guys are figuring in this
out it's it's the most fun time of your
company you get to have these really
energizing conversations with with tons
of users and figure out if they're
potential buyers and good luck because
you'll always look back on this is one
of the most fun parts of your journey so
thanks for having me
and I think we have some time for Q&A
yeah why don't we start here thank you
very much for the talk quick question
you mention about follow-ups and so
forth what would be the appropriate time
between emails and you know just so you
don't feel this you don't seem
overbearing and how I I'd say on average
maybe a little under a week so if you
email someone and they don't get back to
you I think it's you know polite and not
overeager to nudge you know five six
seven days later yeah
oh here hi my name is raisin I was
happiest on sales day at what point
throughout your process did you feel
like you were pestering the customers
you kept you put in a nice way you know
like oh you got to keep on going you got
to keep on asking you got to keep on
sending them along the process did you
ever feel like you were pestering your
customers or not yeah so the question
was do you ever feel like you're
pestering your customers when you send
them follow-up emails I like to think
that if they haven't told you know then
you you know you're within your rights
to follow up you know a reasonable
number of times if you're talking about
emailing someone eight times and they
haven't gotten back to you I mean take a
hint great but you know I think if they
haven't told you know and especially if
you had a earlier conversation where
they were interested you know assume the
best assume they're busy assume that
they've got other things going on you
might not be their top priority but
there's nothing wrong especially if
you're doing it on a you know weekly
cadence or something like that and your
emails are thoughtful and personalized I
have never once in my life been annoyed
by somebody sending respectful
follow-ups as long as they seem
thoughtful and personalized don't forget
that part if it's just like I'm getting
mail merged every week with another
template I mean you know nobody likes
that person but yeah over here
yeah I would say you don't learn about
product market fits from oh sorry the
question was when you're getting these
nose or in early sales conversations how
do you know it when they're just not an
early adopter or an and how do you know
when they're just you should be reading
signs of product market fit or lack
thereof and my answer to that is I don't
think you discover a product market fit
from the nose I think you only discover
it from the yeses
so I think when you get nose there's a
lot of reasons people could give me
giving you nose and I wouldn't even
necessarily believe you know the reasons
that people you know give nose because
in the same way that you can't trust
when VCS give you know you know the
reasons is there's just people struggle
to be upfront and honest and you know
everybody wants to be polite well you
get to product market fit and you know
you have something as when you start
hearing yeses and so you just have to
try and if you can't get any yeses
well there's your signal that you don't
have a product market fit and if you can
get yeses there's your signal that you
do have product market fit and I think
that's all that matters what is the
importance of reference customers in
terms of would you prefer going out to
big brands big names even if they
require far more work than going full
that's know but yeah that's a great
question it is how should you prioritize
big companies which would be amazing
names and logos if you had them as
reference customers or small companies
which might be faster
you know I I think about the advice YC
gives for investors which is to do a
breath for breadth-first search meaning
optimized for speed and optimize for you
know I would say talk to all those
companies talk to the big company talk
to the small company but then you'll
know which ones can can move quickly and
not and optimized for speed a customer
is better than than no customer and the
big companies are never the are never
these great they're great references you
imagine necessarily I would go for who
needs your product the most and who will
move quickly and the reference stuff and
you know the logo stuff you know I don't
think you have to worry about that in
the early days you're just looking for
validation and customers yeah over here
hi area elevate this club I'd like to
hear about your pricing journey and we
have asked of interested customers that
were beginning to now get nervous about
the pricing so one of you about your
journey PS I did had sales at the UCLA
baby bro oh nice oh good to meet you
so your question was about the pricing
journey yeah and how to set pricing that
is a hard question because it's so
specific to every company I'll tell you
what we did at clever we guessed you
know we guess and you get feedback it's
actually kind of neat you get feedback
from the market you know pretty quickly
and you can in the early days you can
iterate you know there's a there's a
Patrick McKenzie likes to talk about how
most startup founders need to charge
more and we'll usually guess too low so
maybe one strategy for guessing would be
to guess a number that seems reasonable
to you and if you can close that sale
you know try doubling it the next time
and if you can close that sale try
doubling it again you it's really hard
to know what customers will pay but I'll
tell you that that you know that
original deal I mentioned for $100,000
that we closed very early on
why was it $100,000 and not you know
half of that or double that it was just
you know us doing a little bit of this
and guessing but we got feedback and you
know iterated from there on the on the
pricing model so I think you just got to
try things be bold
whatever you say you got to believe it
this is the right price for our product
there's no other price would that would
be fair for this you know this thing and
but then quickly you know be willing to
iterate as you get that feedback yeah no
problem in the back there yeah I'm not
sure I understand the question yeah so
yeah so the question is how do you if
you're talking about a $50 price point
for a product how do you and you know
early on in a company's journey how do
you bootstrap a sales effort around that
I mean if you're talking about a $50
product even $50 per month you are
basically basically you probably
shouldn't do any of these things and you
should instead invest in a marketing
function because you are gonna need so
many customers and you know you can't do
it in a high-touch way so you know I
look at things like you know demand
generation and email campaigns and
self-service signup flows and referral
codes and things that you know companies
that that small price point kind of have
to do to be scalable or raise the price
of your product to support you know a
true sales either way but that's
probably how I'd approach it
[Music]
why isn't there anything on your website
yeah there's no product other than the
product that's something I don't talk
okay it sounds like sometimes founders
do this I said what what if there's not
enough case studies on our website for
people to come by
I thought of founders think they're the
net it's never enough whatever they have
is never enough to get people to buy if
they were one had one more reference
account if they had a few more case
studies that's what people you know
that's what it would take for people to
buy guess what if you go on the Wayback
Machine for clever calm from 2012 we
didn't have any case studies you know we
didn't have any customer testimonials
all we had was a page that described the
product and and you know and that was
enough to get you know for people who
had the need they didn't care about any
of that they were like oh finally
someone's built a solution to my problem
great I will run through walls to get it
and we didn't you know we maybe we have
some of that stuff five six years in but
we certainly didn't have it at the
beginning so uh yeah over here sorry one
more time
oh what resources yes the question is
what resources have I learned from you
know in doing sales there is well first
there's no excuse there's no there's no
substitute for doing it I've read a
number of books on sales I've you know
watch things online ninety five percent
of what I've learned has just come from
trying it over and over again and
actually it really appeals to the math
and statistics side of me because you
kind of get to a be test everything yeah
you try something new in a conversation
oh that didn't really work okay gonna
you know try something again
you just get to eater
over and over and over again and so that
is that is the number one way to learn
sales there are some books there's this
one that I love it's called how I picked
myself up from failure to success in
selling it's from like the 1950s and
it's written in this kind of hokey corny
way but it so beautifully encapsulate
the journey of learning sales and you
know some of the hustle and things that
I was describing as part of it earlier
so that's one resource I've recommended
to founders but really you just got to
try it
okay last question yes you look I give a
question hiring salespeople first of all
you have no business hiring salespeople
until you've done a lot of sales on your
own could be good and the reason is not
just you know because of what I was
saying earlier about how you know good
you are it's because you won't even know
what kind of people to hire until you've
done a lot of sales on your own you
won't know what the core skills are is
it is it traveling a lot is it a lot of
phone calls is it a lot of like you know
really good emails you just won't know
once you have done sales for a while the
good news is you'll know exactly the
kind of people that you should hire and
typically that's how I've done it so
I've done sales you know by myself for
three six nine twelve months done made
it repeatable to a to a degree and then
there's you know there's there's
literature out there about what you want
your first sales reps to look like and
oftentimes the term that's used
Renaissance sales rep I and that's kind
of differentiating from the
coin-operated sales rep maybe you know
coin-operated meaning like they they
need everything they need every piece of
collateral every play book every script
but then they can go out and execute on
it just relentlessly on the other side
of that spectrum you have the
Renaissance reps what you needed to
start up and these are folks who don't
need a lot of direction don't need a lot
of playbook and they just
figuring things out and probably your
earliest reps you know even a clever
today I you know we're Renaissance but
you know bigger companies will have much
more on the other end of the spectrum
and so you want to look for those
Renaissance players who can are really
love to learn oftentimes they'll have
some industry expertise but maybe not
too much you know you probably don't
need the person is your first
salesperson who has you know just you
you probably don't want someone you know
don't be too blown away by fifty years
of experience not that that's bad but
it's also you can probably get away you
know if you have the hustle and the grit
that's what's most important at this age
more than experience and so yeah those
are the things I look for is so a lot of
energy a lot of passion kind of that
Renaissance sales rep mentality and then
pattern matching to what I've been doing
in the sales process if they have those
skills great thank you
thanks guys
you
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